


Sam Winchester Shouldn't Quit His Day Job

by Gemilyca3



Category: Supernatural
Genre: Bad Pick-Up Lines, Canon-ish, Destiel - Freeform, Eye Sex, Fluff, Fluff and Humor, Friends to Lovers, Happy Ending, Implied Castiel/Dean Winchester, Kinda season 10, M/M, Matchmaker Sam Winchester, POV Sam Winchester, Sam Ships It, Sam Winchester Ships Castiel/Dean Winchester, Unresolved Sexual Tension
Language: English
Status: Completed
Published: 2018-04-04
Updated: 2018-05-08
Packaged: 2019-04-17 18:59:13
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 8,481
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14195616
Author URL: https://archiveofourown.org/users/Gemilyca3/pseuds/Gemilyca3
Summary: Sam is sick of the sexual tension and conspires to hit Dean and Cas with every tropey set up to finally get them to declare their love.





	1. Did It Hurt When You Fell From Heaven?

**Author's Note:**

> Thanks, again, to ButIAmNotResponsible for being the (non-evil) Metatron to my God!
> 
> This will be updated once a week on Mondays or Tuesdays.

Dean Winchester had always been a miserable son of a bitch, and no one knew it better than his brother, Sam. Raised to be a hunter from the age of four by their widowed father, Dean was a ruthless fighter, but had been left emotionally stunted. John Winchester was by no means father of the year, and it showed in Dean’s personality and behavior. He flitted from woman to woman throughout his early adulthood, never establishing any sort of healthy relationships; even his relationship with Sam was borderline unhealthy and co-dependent. He was constantly feigning happiness but Sam could see that, deep down, his brother was filled with guilt and angst. Sam always thought there was something missing from Dean’s life, but he could never put his finger on it. That is, until they met Castiel.

The Angel of the Lord had entered the Winchesters’ lives about seven years ago when he had rescued Dean from hell. At first, their relationship was touch-and-go. Cas was in and out of touch while they tried to prevent Lucifer’s rising and then the apocalypse, but over the years he still managed to become a regular fixture in the brother’s lives—whether he was trying to kill them, save them, or just royally screwing things up despite his best intentions. The brothers both came to enjoy the angel’s company and were grateful for the extra hand occasionally. But while Sam had forged a strong friendship with Cas, he had to admit that Dean was Cas’s favorite—that they shared a “more profound bond.” Even through their worst patch—Cas’s betrayal—Dean remained adamant that Cas was family and never gave up on him.

Their relationship caused a noticeable change in Dean, who always seemed to have a lighter air about him when Cas was around. The year the brothers were fighting the Leviathan, Dean was one of the most miserable sons of bitches on the planet. Sam was genuinely worried about his brother, who wasn’t sleeping and was drinking more than usual—which was saying something. Sam knew it had to do with Cas’s death, but when questioned, Dean would brush it off, saying he was fine, or he was dealing with it; he hated those “chick-flick moments” and avoided them at all costs. When they finally found Cas alive, Dean’s mood shifted completely, only to have it turn back to misery when Cas was left behind in purgatory.

In the last few years, though, through trials and tablets, Cas had become a much more stable figure in the brothers’ lives and even had his own room in the bunker. Dean seemed to be doing much better with the angel around. Getting the Mark of Cain definitely threw him—threw them all—for a loop, but he seemed to be handling it well; the stability of having the bunker and Cas played a huge part in that. Of course, as much as Sam could appreciate what having Cas in their lives did for Dean, there was a downside: the massive amounts of sexual tension that no younger brother should ever be subjected to.

One particular morning, Sam woke up later than usual and stumbled into the library where, through sleep-filled eyes, he saw Cas and Dean in a moment of— whatever weird heat had developed between the two over the years. It was too early to deal with this shit. This unresolved sexual tension between the angel and his brother needed to become resolved, like, three years ago. He couldn’t handle any more eye-sex and angry flirting. It was obvious to anyone with eyes that the two had some major chemistry between them, and Sam had many theories about why neither of them would make a move: Dean was held up on Cas being in a male vessel, Cas was awkward and inexperienced, the theories went on. Whatever the reason, Sam decided enough was enough. If these two stubborn bastards wouldn’t do it, Sam would make the move for them. This was going to end. Now.


	2. I Like Your Shirt... But It Would Look Better On My Floor

**Summary for the Chapter:**

> Sam starts to put his plan in action.

It had been a week since Sam decided to help Dean and Cas discover their feelings for one another, yet nothing that had happened in the bunker gave him any ideas about how he could subtly show the two how much they meant to each other. It wasn’t until the three of them were getting some lunch at a diner near where they had just taken down a vamp nest that the perfect situation presented itself and sparked an idea in Sam’s head. The waitress stopped by shortly after they sat down to take their orders; Dean ordered his usual bacon cheeseburger and a beer, Cas just had a coffee, and Sam had a salad and a glass of water. The waitress quickly brought the drinks and informed them that their food would be out in a few minutes, and since they had been driving for several hours, Sam excused himself to the bathroom. After taking care of business, he washed up and headed back to the table. When he left the bathroom he saw the waitress was at their table, Sam thought with their food, but as he approached, he realized she was mopping up…beer? Dean and Cas weren’t at the table. Sam cleared his throat as he approached.

  
“Oh, hey!” The waitress stopped wiping down the table and faced Sam. “Your friend spilt his beer. It ended up all over your other friend.” She chuckled at the last part. It didn’t fully explain where Cas and Dean had gone, but Sam figured the pair of them could handle way worse than spilled beer, so he helped the waitress clean up the last of the beer, then sat down to his food. He was halfway through his salad when Dean and Cas came back in. He almost choked on a piece of lettuce when he saw Cas dressed almost exactly like Dean—jeans, an undershirt, and a plaid flannel.

  
“Woah there Sammy!” Dean came around and slapped Sam on the back while he was coughing. “Cas looks good in my clothes, doesn’t he?” Dean winked at Cas and Sam choked even further. He couldn’t believe what he was hearing. Was Dean actually flirting with Cas? This was straight out of a movie; guy sees girl in his shirt and gets all riled up.

  
“Thank you, Dean.” Cas looked around, clearly uncomfortable. He wasn’t used to being dressed like this, since he always wore a suit and his trench coat. The only times Sam had ever seen him out of his uniform was back when he was human. “Are you ok, Sam?” Cas questioned after Sam stopped coughing.

  
“Yea, man. Thanks. Some lettuce just went down the wrong pipe.” Sam paused, trying to word his question carefully. “Why are you in Dean’s clothes? Couldn’t you have just cleaned up with your mojo?”  
“He was about to, but the waitress had already started walking over,” Dean answered through a mouthful of burger. “Didn’t want to raise any suspicion.”

  
Sam nodded with understanding, turning his focus back to his food. The three of them sat in relative silence for the rest of their meal. Sam kept thinking about the way Dean looked at Cas in his clothes, the way he flirted so openly. That was closest he could ever remember Dean getting to admitting his feelings—with the exception of near-death experiences. Maybe…maybe that’s just what Dean needed. Not another hunt or world-ending scenario, but a simple romantic setup. And Sam could provide that easily, couldn’t he? He hadn’t realized that his train of thought left him staring at Cas until Dean called him out on it.

  
“Dude, what’s up? Why are you acting weird?” Dean gave Sam a questioning look. “What, you got the hots for Cas now?”

  
Cas looked up from his coffee, a blush rising on his face and his eyes wide with worry. Sam ignored the question and continued to eat his salad in silence. This was going to be harder than he thought. Dean and Cas’s denial about their feelings for one another ran deeper than expected.

  
The following morning, once they were back at the bunker, Sam woke up early, the events of yesterday still on his mind. He sat in bed musing the situation and how he could help his brother and best friend be happy together. Once he got out of bed, he headed straight for the kitchen; developing a plan was going to take enormous amounts of coffee. Once thoroughly caffeinated, Sam went to the war room to start doing research. Getting these two stubborn asses to realize their feelings and actually make them ‘fess up to it was going to be tricky. As farfetched as the idea was, Sam thought maybe he could take some hints from some of the chick-flicks that Dean denied loving, along with some of Dean’s cheesiest pick-up lines. Maybe if he got the two into close enough contact, they would stop denying their feelings. Sam sat at the table for a good long while, listing every trope he could think of, then narrowing it down to just the ones he thought would work on Dean and Cas. All he had to do now, was wait for more opportunities to present themselves.


	3. You Must Be One Spicy Dish Because You're Making My Heart Burn

It had been weeks since the incident at the diner and, despite the spark in Dean’s eyes when Cas ended up in his clothes, nothing had changed. Sam still caught them staring at each other and bickering like an old married couple, but never saw any hints of romance. Fortunately, Sam already had a scenario in mind that he was sure would push Dean and Cas into discussing their feeling. Sure, it was going to be a bit complicated to pull off, but would be absolutely worth it if it worked.

They pulled into the motel parking lot after another successful hunt. They were staying at a place that was a little nicer than their usual digs, which had taken some persuading, but Sam had put up a convincing act.

“Come on, Dean. Just once I would like to sleep on a decent mattress!” Sam argued. “Plus, it’s not that much more a night than we usually spend.”

Dean rolled his eyes, but didn’t say anything more. Sam knew Dean would give in; he was a sucker for a good mattress.

“Dean, Sam has a point. You know how your back gets when you don’t get a good night’s sleep.” Cas spoke up. “A decent mattress would do you good.”

“Fine.” Dean blushed slightly before conceding. “You two win. We can stay at the fancy friggin’ hotel.”

“Wait, really?” Sam arched his eyebrows as he looked between Dean and Cas. Did Dean say yes just to please Cas? Maybe Sam was on the right path and Dean would admit his feelings sooner rather than later.

“Yeah, yeah. Whatever.” Dean rolled his eyes again. “Let’s just drop this and hit the road.”

There was an Italian restaurant attached to their motel; one of the perks of staying at a nice joint. It also happened to be the main reason Sam chose this motel to stay at. He was hoping to set Cas and Dean up on a first date of sorts. Maybe a little romantic atmosphere was all they’d need to break out of the holding pattern they’d been stuck in…but getting them there without him was going to be tricky.

“Oh, hey,” Sam causally started “How ‘bout we grab some food at the motel restaurant?” He didn’t have to press much as Dean never turned down an opportunity for food.

“Hell yes! I’m starving.” Dean smiled enthusiastically from the driver’s seat and turned towards Sam.

“Dude!” Sam yelled. “Eyes on the road!”

They pulled up to the motel and parked in front of their room. The three of them got out of the Impala and unloaded their gear into the room before making their way to the restaurant. When they walked inside, they were greeted with the smell of tomato sauce and the sounds of hokey Italian-American songs. They walked up to the hostess booth—the young woman was a perky blonde with dark eyes; she was definitely Dean’s type. Sam was expecting to have to fend Dean off, but was surprised when he didn’t turn on the charm, even when the hostess winked at him.

“Welcome to Nonna’s Cucina. Table for three?” She looked Dean up and down, before giving him a seductive smile. Sam immediately pushed his way between Dean and the hostess.

“Yes!” He said a little too enthusiastically, resting his elbows on the podium and giving her a wink. She gave him a confused look at first, startled by his strange behavior.

“Right this way, sugar.” She said, returning another flirtatious smile, this time towards Sam.

“You sly dog!” Dean elbowed Sam as he grabbed Cas’s shoulder and guided him to their table, following the hostess.

Sam sighed with relief that he wouldn’t have to fend Dean off the young woman. Once they reached their booth, the hostess placed three menus on the table and informed them that their waiter would be with them shortly. Dean and Cas sat down next to each other, Sam sliding into the bench opposite them. He was only sitting for a minute or two before he decided it was time to leave.

“Actually, you guys. I’m not really feeling super great.” Sam wrapped his arm around his stomach, hunching over. “I don’t think that sandwich I ate at lunch is agreeing with me.” He got up and left before Dean could say anything or figure out that he was faking it. On his way out, Sam stopped at the hostess booth again.

“So, it’s my brother’s anniversary with his boyfriend and I wanted to do something nice for them. I was wondering if you could maybe bring them a bottle of wine?” Sam pushed a twenty towards the hostess.

“Aww,” the hostess pressed her hands to her chest. “That’s so sweet of you! You’re such a supportive brother. I’ll see what I can do.”

“Thanks.” Sam gave her another flirtatious smile. “Oh, one more thing… my brother is really shy, so could you not make a huge deal out of it or let them know that I set this up? Maybe just tell them it’s on the house?”

“Of course.”

Sam thanked her again and said goodbye. She winked at him as he left.

An hour later, Sam was lying in bed, reading _A Storm of Swords_ , when Dean and Cas came through the door. Dean was slumped over Cas. It would appear that the hostess followed through on the bottle of wine.

“How was dinner?” Sam asked with a smirk.

Cas only huffed and rolled his eyes in response, a scowl resting on his face as he tried to keep Dean from stumbling around, to no avail. Dean pushed himself away from Cas, lurched across the room, and fell on the bed. The angel was left standing in front of the bed, arms crossed; he was clearly not happy.

“What’s up, Dean? Did you not have a good time, ‘cus it sure seems like you did.” Sam asked, holding back a laugh. Dean made a muffled sound, his face buried in the mattress. Sam gave Cas a questioning look, hoping the angel was able to decipher the message.

“He’s mad because they didn’t have any pie on their dessert menu. Though the waiter seemed ready to go and fetch some for him specially.”

Dean turned his head so he could be heard. “I can’t help that I’m adorable and everyone wants a piece of me. I just wanted a piece of pie.” He huffed before turning his head back to the mattress. A few minutes later, soft snores could be heard from the lump of hunter on the bed.

“The waiter was flirting with Dean?” Sam asked, but Cas didn’t reply, just stalked over to turn on the crappy TV. Now Sam was left upset, too, frustrated that even putting Dean and Cas in the most date-like situation he could engineer wasn’t enough for them to finally admit that they were practically a couple anyways. Next time he’d have to make sure there weren’t any flirtatious waiters around, at the very least.


	4. Do I Know You? Because You Look Exactly Like My Next Boyfriend

**Summary for the Chapter:**

> Sam continues to try and set Dean and Cas up in romantic situations in the hopes that they will realize their feelings for one another.

They needed to get out of the bunker. Things had been quiet lately and Sam and Dean were going stir-crazy—not to mention how Sam was still stuck in the middle of the unresolved sexual tension and heated eye-sex between his brother and the angel. He’d escaped to the library of the bunker to search the news for any signs of a case, and had come across an interesting article just as Dean walked into the room.

“So get this,” Sam started, not even bothering to look up from his laptop. Dean walked over to Sam and pulled up a chair. “Four bodies, throats slit, drained of blood, but no blood at the crime scene.”

“Sounds like vamps to me!” Dean pushed back in the chair. “I’ll grab Cas and we can head out.” He stood up and walked out of the library.

They were on the road in no time and pulled into a dingy motel parking lot several hours later. After getting their standard four hours of sleep, Sam, Dean, and Cas went to the morgue to check out the bodies. In addition to the usual vampire markings, they also found an odd symbol inked on each of the victim’s wrists. Sam volunteered to research the symbol, so Dean dropped him off at a diner and then went with Cas to play FBI at the police station.

Sam snagged a large booth at the diner and pulled out his laptop and a hastily scrawled drawing of the symbol. When the waitress—Shelby, according to her name tag—showed up at his table, he asked for the wi-fi password and ordered a soda and some fries. Once he logged on, Sam set to work looking up the mark. Shelby dropped of Sam’s food and drink and hung around for some small talk; she was nice, and friendly, and seemed to be infatuated with Sam.

“Oh, that looks familiar.” Shelby paused, her hand resting on Sam’s shoulder as she glanced at the drawing on the table.

“Do you know where it’s from? I’ve been trying to find out but haven’t found anything.” Sam ran his hand through his hair.

“Yeah. I’m pretty sure that’s the cover stamp from this club downtown. The—The Library? I think it’s called.”

Sam looked up at her with surprise. “Wow. Thanks!”

“No problem. It’s the only gay bar in town; I’ve heard it’s pretty difficult to get in.”

Sam nearly choked on his drink. “Wait. A gay bar, are you serious?” Shelby’s face took on a look of offence but Sam was already barreling on. “This is perfect! I’ve been trying to get my brother and his buddy together. This might just be the set-up they need!”

Shelby let out a sigh of relief and chuckled. “Good luck, then. I’ll bring you some more fries.”

Just as Shelby was coming back with the fries, Dean and Cas entered the diner and quickly slid onto the bench across from Sam. Dean didn’t even say “hi” before grabbing a handful of fries and looking up at the waitress.

“Hey, gorgeous.” Dean winked at her. “Can I get a bacon cheeseburger with fries? My devilishly handsome friend here will have the same,” he said, pointing to Cas.

“Sure thing.” Shelby chuckled as she walked away to place their order.

Dean grabbed another handful of fries, shoving them in his mouth. “You figure out that symbol?” Dean mumbled through a mouth of half chewed food.

“Uh, yea.” Sam cleared his throat. “It’s a club downtown called The Library. I figured we could go check it out tonight.”

“Hahaha. The Library,” Dean elbowed Cas, laughing. “Must be a whole club for nerds. Sammy will feel right at home!”

Sam bit back several responses that sprang to mind. The longer he could keep Dean from knowing that it was a gay bar, the less chance Dean would have to protest…but Sam was definitely looking forward to seeing Dean’s face when he figured out the truth. In the meantime, he had some planning to do, especially since he didn’t want a replay of someone else hitting on Dean in front of Cas. He wasn’t quite sure how he was going to play it, but he figured there would be plenty of opportunities at the club.

After finishing up at the diner, the three hunters went back to the motel to get ready for their evening out. Dean had come out of the bathroom in his usual get up of jeans, plaid flannel, and his canvas jacket but Sam convinced him to put on something nicer with the argument that most night clubs require certain dress codes.

“Man! Why do I need to change?” Dean didn’t want to put his monkey suit back on—he hated wearing that thing.

“Shelby said it’s difficult to get in. I thought if we dressed up a bit, we’d have a better chance.” Sam buttoned the cuffs of his own dress shirt. He needed Dean to look nice; he was banking on Cas recognizing Dean’s attractiveness and making a move tonight. Sam realized there were a lot of unknown variables and he was doing a lot of hoping, but he was sure the situation would provide the much-needed push the couple needed to, well, be a couple.

“Oh! Well then, if _Shelby_ told you, I guess it must be true!” Dean huffed and grumbled before going back to the bathroom to change into his fed suit slacks and a button up. “Fine. But I’m not wearing the tie!”

Cas remained in his standard suit and trench coat—he only had the one outfit, so his choices were limited. When Dean emerged from the bathroom, Sam noticed Cas’s reaction. _Yes_ , Sam thought to himself, _this might actually work._

The line for the club was around the block when they got there, which caused Dean to whine even more: “Man, this line is too friggin’ long… There are hardly any chicks here… Dude, that guy keeps staring at your ass...” Sam was getting sick and tired of Dean’s immaturity when they finally hit the front of the line. The bouncer looked them over and told them they were going to have to wait a little longer. Sam couldn’t handle any more from Dean so he decided to convince the bouncer to let them in.

“Please, man. We’ve been waiting all night.” Sam put on his best puppy dog eyes—no one could resist them. “It’s my brother-in-law’s birthday and we just want him to have a good time.”

Dean started sputtering behind Sam and Cas tilted his head in confusion. The bouncer rolled his eyes but unlatched the rope and stood aside.

“Happy birthday,” he said to Cas as he walked into the club.

Sam thought the drama would stop once they got into the club, but as soon as they walked inside Dean grabbed Sam’s arm, forcefully.

“Dude! What the hell was that about.” Dean was doing a poor job suppressing the rage in his voice. “Cas and I are not married! Why would you say that?”

“What?” Sam shrugged his shoulders, putting on an air of innocence. “We needed to get into the club. And, hey, it worked didn’t it?”

The anger in Dean subsided for a moment until he realized what happened. “Wait, are you telling me this is a gay bar?”

“Oh, did I not mention that earlier?”

“No!” Dean flung his arms out in frustration.

“It’s fine, Dean.” Cas placed a hand on Dean’s arm, instantly calming him.

Sam rolled his eyes for the tenth time that evening and turned towards the bar. “Cas, why don’t you go grab us some drinks and a table. Dean and I will ask around if anyone’s seen anything weird.”  

Cas made his way to the bar. Dean pouted for another minute before walking off, Sam trailing behind. They made their way around tables, trying to casually ask people about the murders, until they found a couple of regulars who were more than happy to answer questions. Everything was going smoothly until one of the men they were talking to mistook Sam and Dean for a couple.

“Aww. You two make a cute couple,” the man said with a smile, placing his hand on Dean’s shoulder.

“Oh, um…” Sam stumbled over his words. “We’re—we’re…”

“Thanks,” Dean wrapped his arm around Sam and pulled him close.

Sam’s face dropped into a scowl. This was not going well; Dean and Cas should be mistaken for the couple, not him and Dean. They were brothers, for god’s sake!

“Uh,” Sam cleared his throat. “Thanks for your help. We better get going. Come on, Dean.” Sam grabbed Dean’s elbow, pulling him away, but quickly dropped it when he heard a chorus of _awws_ coming from behind. Sam stormed off, finding Cas at a standing table, staring off into the crowd.

“What the hell, man?” Sam turned to Dean as he walked up to the table.

“What?” Dean shrugged with a laugh. “I was just trying to get information. Same as what you did to get us in here.”

Sam grumbled and grabbed his beer, draining it in a few gulps. He was about to yell at Dean again, when he was interrupted by Cas.

“What happened?” The angel cocked his head to the side in his usual, confused manner.

“Oh, nothing.” Dean patted Cas on the shoulder and reached for his own beer. “Sammy’s just upset because someone mistook us for a couple, again, and I didn’t correct them this time.”

“Whatever,” Sam said as he angrily dropped his empty glass on the table. “I’m going to go get another beer and see if I can’t get any more information from the bartender.”

Dean and Cas had disappeared by the time Sam got back to where he had left them. He figured they had spotted something and were investigating. Sam pulled out his phone to text Dean.

**_Sam:_ ** _Where’d you go? I got a description from the bartender._

He pushed send and waited for a response. He stood at the table, drinking his second beer at a more reasonable rate this time. His eyes scanned the crowds, looking for any signs of his brother and the angel. He waited for a response, to no avail, so he sent another text, to Cas this time.

**_Sam:_ ** _Hey, Cas. Where are you and Dean? I can’t find you. Text me back._

**_Cas:_ ** _We’re in the back of the club._

Sam headed towards the back of the club but stopped dead in his tracks when he spotted them. Dean was fast asleep against Castiel’s shoulder. Sam reached his hand in his pocket to pull out his phone for a picture—it would be great for blackmail—when Cas spotted him, waving him over.

“Hey,” Sam greeted the angel. “What happened?” He gestured to the sleeping hunter.

“Dean fell asleep.” Cas had his usual, unreadable face on.

“Yea, Cas. I can see that.” Sam chuckled. “Why did he fall asleep? Did he have too much to drink?”

Before Cas could answer, Dean stirred, mumbling in a half-asleep state. “Wha—wha’s going on?”

“You ready to head out? I got some information we can go over at the motel.”

Cas nodded. He turned to Dean, who had fallen back asleep, whispering to wake him up. Dean sat up, eyes groggy with sleep, as Cas wiggled his shoulder.

“Come on, Dean,” Cas whispered. “We’re leaving.”

Sam helped sleepy Dean to his feet. Once Cas was standing, he resumed his task of holding the elder hunter up and guiding him back to the car. Cas maneuvered Dean into the back seat and slid in next to him while Sam took the driver’s seat. Before he pulled out of the spot, Sam glanced in the rear-view mirror and saw Dean, back asleep, resting on Cas’s shoulder. He might almost have called it cute, except that he knew the moment Dean was awake again it would be back to their usual program of denial and longing. After all the frustration this matchmaking plan was causing Sam, he was almost feeling grateful to have a simple task like beheading vampires ahead of him.


	5. You Look Cold... Want To Use Me As A Blanket?

**Notes for the Chapter:**

> Sorry for the late post. I lost track of the days :( Hope you're enjoying the story.

Their next case was in a small town outside of Chicago where they had heard signs of a Lady in White. By this time, winter was in full swing; the snow was ten inches deep and it was cold as balls outside, so they spent their time between the tiny public library and the only motel in town, keeping the legwork to a minimum. It was difficult for hunting monsters, but perfect for Sam’s next scheme—which didn’t involve anyone else butting in and ruining it. All he had to do was hang back at the motel while Dean and Cas went out to the library—the actual library, this time.

“Dude. You love the library! Why do you want to stay here?” Dean asked, confused.

“Well, I’m kinda on a roll right now,” Sam lied, not looking up from his laptop. “I want to finish up with this surveillance video.” Sam was hoping he was being convincing enough for his brother to drop it.

“Fine. Whatever.” Dean rolled his eyes and turned to leave. “Come on, Cas. Let’s hit the books.”

Dean headed out the door, Cas following closely behind. Sam heard the muffled rumble of the Impala’s engine quickly fade. Finally, they were gone. Now Sam could put his plan into action—time to disable the heater. He realized that this was going to slightly punish himself, but he had come prepared with extra blankets, and it would be so very worth it if it finally worked. He pulled out some tools he had stashed in his bag and got to work tampering with the heating system. Sam had just finished breaking the heater when Dean called to say they were on their way back. He and Cas had figured out who the Lady in White was and they were going to pick up Sam and go “gank the skank”.

By the time Sam, Dean and Cas came back from the hunt, the room was a balmy 58 o and quickly dropping.

“What the—” Dean shivered as he walked into the room. “What the hell happened, man?! It’s freezing in here!”

Sam and Cas followed Dean inside. “Oh yea, the heater went out or something.” Sam scratched his head, trying to act casual. “I called the front desk all afternoon, but they said they weren’t going to be able to get someone to fix it until tomorrow.”

“Well, let’s go see if they have another room then.” Dean headed back towards the door, pulling his jacket tighter around him.

“No!” Sam yelled, louder than necessary, startling Cas. “I mean—I already asked. They’re booked.”

Cas tilted his head in confusion. “The sign outside says ‘vacancy,’ though.”

“Um,” Sam cleared his throat, thinking. “Yea, they—they only had singles left.”

Dean eyed Sam suspiciously; there was something weird going on. Granted, his brother was definitely strange, this was more than usual. “Well, I’ve got some tools in the trunk,” Dean said as he walked out the door. “Lemme see if I can fix this damn thing.”

Dean shuddered as he came back into the cold room, bag of tools in hand. He dumped the bag next to the heater and set to work. Dean spent over an hour trying to fix the heater to no avail, since, unbeknownst to Dean, Sam had anticipated this and stolen one of the capacitors so that no matter what Dean tried, it would still be broken. Sam was not going to let them weasel their way out of this plan!

“Damn it!” The frustration was evident in Dean’s voice as he threw the wrench he was using at the wall.

“Give it a rest, Dean.” Sam put on his best annoyed voice, which wasn’t too far off from the way he was actually feeling. “Just accept that it’s going to be a cold night! Hey, maybe you and Cas can use each other for body heat!”

Dean rolled his eyes and took a deep breath, probably thinking _Do not punch Sam, do not punch Sam._ “I’m—I’m fine, man.” There was the usual, uncomfortable edge to Dean’s words. “I’ve got a sweatshirt and the comforter will be enough. Plus, Cas doesn’t sleep; he would be bored out of his mind.”

“I could watch over you while you sleep, Dean. That is never boring to me.” Cas looked at Dean who was obviously trying to refrain from yelling his usual _that’s creepy, Cas_. Cas must have seen it coming, so he quickly changed the subject. “Plus, I do not feel cold. With my grace, I am able to regulate the temperature of my vessel. I have no need to use Dean for warmth.”

“Fine, suit yourselves, but I’m not sharing my blankets!” Sam grumbled, discouraged, as he burrowed farther under his blankets. Why was this not working? How stubborn and dense were these two? Maybe they were hesitant to share a bed with Sam in the room. With these thoughts, Sam quickly drifted off into sleep.

By the time Sam woke up the next morning, the sun was high enough to have warmed the room to a comfortable temperature. He sat up in bed, pushing the excess blankets off. He turned to see Dean, still sleeping with several new blankets piled on top of him. _Huh._ Cas was sitting on the couch doing something on the laptop. _Figures_. Sam signed in defeat that his plan had, yet again, failed.

“Morning, Cas.” Sam yawned, stretching his arms above his head. He turned and got out of bed, stumbling over to the coffee maker.

“Good morning, Sam.” Cas barely looked away from the computer. “I trust you got a restful night’s sleep, despite the cold?”

“Uh, yea. The blankets helped.” Sam poured himself a cup of coffee. As he sat down at the table, he remembered he had stashed the missing capacitor in his duffle bag. He sighed and figured he might as well let Dean fix the heater as they were planning on leaving the motel later that afternoon. There was no sense in letting the next guests suffer through the cold. He pulled the missing piece out of his bag, setting it on the table. He would tell Dean he found it by the heater once Dean woke up. Sam finished his coffee and moved to the couch with Cas. The two worked on some leads for their next case. An hour or so later, they heard rustling and Dean stumbled out of bed.

“Good morning, Dean.” Cas turned as he greeted the elder hunter.

“Morning” Dean grumbled, rubbing his eyes. “Thanks for the blankets, man.”

“You’re welcome, Dean,” Cas said with a smile, turning back to the laptop. Sam sat there staring at Cas. He must have gone out in the middle of the night to get blankets for Dean. _Interesting_ , Sam thought. If Cas was willing to go out of his way to make Dean comfortable, then he obviously liked the guy. Normal friends don’t go out in the middle of the night to get blankets for their buddies. Why couldn’t Dean see how Cas felt about him? Why wouldn’t Cas just make a move already? Since Sam had embarked on his plans to selflessly help Dean and Cas get their shit together, he had missed out on a rare chance for a halfway decent meal, had to pretend to be dating his own brother, and now nearly frozen to death overnight, and absolutely nothing had changed between Dean and Cas. If Sam weren’t so stubborn, he might just give up now, but there had to be _something_ he could do…he’d give it one more shot. One _last_ shot.

 


	6. Your Lips Look So Lonely... Would They Want To Meet Mine?

In order to make his last, desperate attempt to get Dean and Cas to admit their feelings for one another, Sam had instigated a purge. That is, he’d taken advantage of a lull in hunting to rope Dean and Cas into doing some spring cleaning in the bunker. While they had gotten through most of the archives when they first moved in, they had been discovering more and more unorganized artifacts as they continued to explore. Sam wasn’t planning anything fancy this time; all he had to do was get them into the same room and he would go middle school on their asses and lock them in until they had their seven minutes in heaven. He had already done the research to get a spell to keep the door locked and the proper warding to stop Cas from busting down the door with his angel mojo.

“Cas!” Dean’s voice echoed through the bunker. “Cas, come in here and help me.”

Cas sighed as he got up from the table where he and Sam were categorizing some of their new literary findings.  

“What does he want?” Cas questioned.

“I think he was cleaning out one of the storage rooms that had a bunch of unlabeled boxes.” Sam glanced up from the pile of books he was working on, but Cas had already disappeared down the hall.

Sam waited until he heard Dean mumble orders to Cas to help him move some of the heavier boxes.  Once Sam was satisfied that the two were occupied enough to not notice him, he grabbed the ingredients for the spell and paint for the warding, and quickly got up from the table and carefully walked down the hall. Sam peered into the room to make sure they were busy enough moving boxes around to not hear Sam close the door and lock it.

Sam set about putting up the warding and casting the spell. There was no way those two were going to be getting out without Sam’s permission. Once everything was set up, Sam went back to the library to continue his sorting. It wasn’t too much later when he heard rattling and pounding coming from the closet.

“Sam!” Dean was shouting. “Sammy! Get your ass over here!”

“Hey, Dean. What’s going on?” Sam spoke through the door once he reached it.

“Sammy, the door is stuck. Let us out!”

“Huh.” Sam pretended to wiggle the doorknob. “That’s weird. Did you mess with something that could have locked you in?”

“No!” Dean pounded against the door again. “Cas can’t even mojo the door open!”

“Sam,” Cas spoke sternly through the door. “There’s some kind of warding preventing me from using my grace.”

Sam smiled to himself. _This was going well_ , he thought. Everything was going according to his plan. Now all he had to do was stall with getting the door open, so the two would have time to be in each other’s company. He wiggled the doorknob again.

“You know what? I think I see some markings on the door here, but they’re really faint. I’ll be right back. You two just—uh—hang out or something. I’m going to look through some of the Men of Letters records to see what this room was used for!” Sam yelled back as he headed to the library.

“Sam. Sammy!” Dean’s muffled yells followed Sam down the hall.

A few minutes later Sam returned to check on Dean and Cas. He was trying to be quiet, but Dean must have heard him because he started yelling again.

“Dude!” Dean yelled through the door. “What’s going on?”

“Calm down, Dean.” Sam rolled his eyes. “I’m still going through the archives.”

“Come on, man. Just bust down the door! Use the grenade launcher!”

“No way! That’s too dangerous. I just came over to get a rubbing of some of the markings.” Sam scratched at the door, pretending he was making the rubbing. “I gotta make a call about this symbol. I’ll be back.”

Once back in the library, Sam was about to go back to cataloging the books when he realized that with Dean out of the way he could do anything he wanted. It had been a while since he had time to relax, so Sam went back to his room to lay down for a while; he was almost done with the book he was reading and with Dean occupied, this happened to be the perfect opportunity to finally finish it. Reading gave Sam another idea: he was out of books to read, especially since Dean was always stealing them. Maybe a trip to the bookstore was needed. At that moment, his stomach rumbled, and he realized he never ate lunch. Sam wandered into the kitchen only to discover that they were in desperate need of a grocery run. Lunch, bookstore, then grocery store—that was the plan. Back in the library, Sam found the keys to the Impala in Dean’s jacket pocket.

“Haha,” Sam chuckled to himself. Dean wasn’t here to stop him from taking his baby. Sam stopped at a diner down the street from the bunker and scarfed down a salad before going to the Goodwill for some books. He found several that he thought sounded interesting and would probably make their way into Dean’s room at some point, although Dean would never admit to it. On his way out of the store, Sam noticed what a nice day it was and ended up driving to the nearby park instead of going back to the bunker. He walked around the park for a bit, soaking up the sunlight and people watching. He even got to pet a few dogs that were running around. Sometimes he wished Dean was more of an animal person; a dog would be a nice addition to the bunker. When Sam looked at the time, he realized he had been out for far longer than anticipated. On his way back to the bunker, Sam made a pitstop at the grocery store. He went through the aisles grabbing food Dean usually wanted, but then it occurred to him, he could get whatever groceries he wanted. Hello wheatgrass smoothies and garden salads! Alright, he would keep some of the food Dean liked; he wasn’t that mean of a brother.

Silence greeted him when he walked through the bunker door. Cautiously, Sam approached the locked room, calling for Cas and Dean. Silence. It was only when he was right next to the door, fist raised to knock on the door, that his brother finally answered.

“We know you locked us in here, Sammy.” Dean’s voice was loud, but unusually calm. “Now let us out.”

Sam stood there for a moment, suddenly worried about Dean’s retaliation once he was let out.

“Neither Hell nor Purgatory could hold me for long, Sam Winchester. Don’t for a second think that you will be more successful.”

Now that was something to be afraid of; Cas was an almighty, celestial being, and sometimes Sam forgot. To avoid further angering an experienced hunter and a powerful angel, Sam decided it was time to let them out.

“Ok. Ok. I’ll let you out,” Sam sighed with defeat. “I just need to grab some ingredients for the spell and I’ll be back. I promise, this time.”

Sam removed the spell and the warding in no time and braced himself for retaliation. Dean and Cas burst through the door.

“Damn it, Sam!” Dean slammed his palms at Sam’s shoulders, shoving him backwards; he was livid. “What the _hell_ is wrong with you?! Why did you lock us in there? I thought we had tripped some weird, Men of Letters alarm and then you disappeared for over an hour! We thought whatever tripped the alarm got you.”

Sam rubbed his shoulder, a surprised look on his face. He had not expected Dean to react so violently. Sam looked down, avoiding eye contact with his brother.

“Sorry? I was just pulling a prank?” Sam’s response came out more as an unsure question rather than a convincing statement.

“Grow up, man.” Dean punched Sam’s shoulder again before storming off to his room. The door slammed shut causing Sam to flinch. He was going to be getting the cold shoulder for days after this. Cas brushed past him, heading down the hall. Sam slid down the wall to the floor, resting his head in his hands. How did he screw this up so badly?


	7. I'm Mr. Right. Someone Said You Were Looking For Me.

**Summary for the Chapter:**

> Sam's shenanigans finally come to a conclusion.

**Notes for the Chapter:**

> Whelp. This is the last chapter. Thanks to everyone who read this and left comments or kudos. I hope you all have enjoyed this story as much as I have. :)

Sam sat at the table in the library, lost in thought. He still didn’t understand what he’d done wrong. It had been over a week since the closet incident, and Dean was still acting strangely. Not only was he ignoring Sam, but he was even a little on edge with Cas. How could all of Sam’s attempts to bring Dean and Cas together have wound up driving a wedge between them? Then it occurred to him…maybe, it wasn’t him. Maybe it was them! Maybe the reason his set-ups weren’t working was because Cas, while having vastly improved, still wasn’t that in-tune with human customs, which could have caused him to not pick up on many of the situational cues Sam’s plans had offered up.  Fortunately, Cas wasn’t ignoring Sam—in fact he was reading quietly on the other side of the library. If Sam’s latest train of thought was right, they could clear it up pretty quickly.

“Hey, Cas.” Sam spoke up, just a little hesitant. “Can I ask you something?”

“Of course, Sam. You know you can always talk to me.” Cas set down his book and stared patiently at Sam.

“Um…” Sam trailed off; he wasn’t quite sure how to broach the subject but decided to just go for it. “How would you go about showing someone you liked them?”

Cas tilted his head. “I don’t understand the question.”

“Well, let’s say you had romantic feelings for someone. How would you let them know?”

“I—um—” Cas stuttered, obviously flustered by the question. “Sam, is that a flirtation?”

“Seriously?!”

Of course, Dean would choose that exact moment to walk in the room. He hadn’t left his room in days, but decided to be social at that exact moment. Sam buried his face in his hands and groaned.

“Sam!” Dean yelled. “Come on man, what’s going on?”

“Nothing, Dean. I just—” When he caught Dean’s stern eyes, he reevaluated his response. “Um…” Sam cleared his throat in hesitation before continuing. “Ok. Fine. It’s just that… You and Cas. There’s obviously something there between you. And well, Dean, you’re always happier when Cas is around and I just wanted you to realize that you two have feelings for each other!”

“Wait. So, let me get this straight.” Dean’s eyes were closed and he had his hand held up towards Sam, a gesture that told Sam to shut up. “The last few months… The wine at that restaurant, the heater going out, the gay bar, locking us in the closet.” Dean laughed when he finally put two and two together. “You set all those things up… You—you were trying to set me and Cas up?”

Sam turned his puppy dog eyes downward with a guilty shrug and prepared for the yelling to start, but his expression turned to confusion when he was surprised with the sounds of a deep chuckle. When he looked back up, Dean had his head thrown back and was laughing hard. Sam wasn’t sure if this was an angry laugh and prepared for the worse, but when Dean started talking again, Sam realized it was an actual, happy laugh.

“Dude! Cas and I have been a couple for like,” he paused and looked at the angel. “What like over a year now, Cas?”

“It will be one year and five months next Friday.” Cas confirmed with a smile. “And the sexual tension was resolved shortly before that, when Dean saved me from the Rit Zien.”

“Hey, man!” Dean scolded Cas. “You don’t have to give him all the details.”

Sam stared at them, his chin almost on the floor. “Wait… So… You two… What?”

“Yea, man. I thought you knew. I mean it was definitely rough for a while, especially with Cas losing his grace then getting it back and Gadreel and the Mark of Cain...” Dean rambled. “But, I mean, we weren’t flaunting it, but we weren’t trying to keep it a secret either.”

Sam stared at Dean, awestruck. How had he not seen it? The signs were there—Dean’s ease with Cas in his personal space, not being phased by the gay club, Cas being jealous when the waiter flirted with Dean. Sam’s jaw dropped at the realization. “How did I not see it before?” He pondered.

“What kind of clue did you need, man? A wedding invitation?” Dean’s laugh stopped abruptly when he realized what he said.

“Yes!” The frustration was clear in Sam’s voice.

“Oh,” Cas joined the conversation again. “Are we getting married, Dean? I thought your proposal would have been a little more romantic… but… of—”

“What? No. I mean…” Dean cut Cas off before he could continue. Dean was obviously flustered and Sam was loving it. “That’s—no— that’s silly, Cas. Cus, you know, I’m legally dead. And—and you’re—you don’t exist to the government. It’s not like we could just go down to City Hall and get a marriage license.” Dean’s face was reddening by the second as he stumbled over the words. “Plus, it’s just a silly piece of paper. We don’t need that to know how we feel about each other.”

Dean scratched the back of his head, pushing past Sam and Cas as he fled the room. Sam was practically on the floor, laughing.

“Oh, man, Cas!” Sam pressed his hand to his chest, trying to breath. “Dude, I’m sorry you have to put up with that!”

Cas stood there, baffled at the exchange. Sam watched the gears turn in the angel’s head.

“Sam,” Cas said, turning towards Sam. “You support our relationship?”

“Of course!” Sam patted Cas on the shoulder, trying to reassure him that he was ok with it. “You know I love you like a brother.”

“And you were willing to invest great energy in helping Dean and I admit our affections for one another?”

“Haha, yea.” Sam chuckled as he cleared his throat. “Not that you needed it, apparently.”

“But you did display a certain level of tactical ability.”

“Uh…” Sam arched his eyebrow, curious as to where the angel’s line of thought was headed. “Thanks, I guess?”

“Sam,” Cas said with his usual serious face. “I need your help getting Dean to marry me.”

**Notes for the Chapter:**

> Ok. So there might be a sequel eventually... ;P


End file.
